syn-methyl-2,3-dihydroxy-2,3-diphenylpropanoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: syn-methyl-2,3-dihydroxy-2,3-diphenylpropanoate
• 英文别名: methyl 2,3-dihydroxy-2,3-diphenylpropanoate；anti-methyl 2,3-dihydroxy-2,3-diphenylpropanoate；(2RS,3SR)-2,3-dihydroxy-2,3-diphenyl-propionic acid methyl ester；(2RS,3SR)-2,3-Dihydroxy-2,3-diphenyl-propionsaeure-methylester；methyl (2S,3R)-2,3-dihydroxy-2,3-diphenylpropanoate
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: HXAQRWJWDVFXJU-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 aqueous acid 作用下， 生成 syn-methyl-2,3-dihydroxy-2,3-diphenylpropanoate
  参考文献：
  名称：

  The Reactions of Halogenated Ketones. II. The Action of Potassium Cyanide on Desyl Chloride

  摘要：

  DOI：

  10.1021/ja01337a074

文献信息

• Efficient diastereoselective synthesis of α,β-Dihydroxyesters from methyl phenylglyoxylate and aldehydes mediated by Titanium Trichloride/Pyridine System
  作者：Angelo Clerici、Laura Clerici、Luciana Malpezzi、Ombretta Porta

  DOI：10.1016/0040-4020(95)00872-6

  日期：1995.11

  The reductive coupling of methyl phenylglyoxylate 2 with aliphatic and aromatic aldehydes 3, promoted by TiCl3/Py system in anhydrous THF. affords α,β-dihydroxyesters 4 in good yields (60–94%) and high syn-diastereoselectivity (up to 85%) The type of ligand at the metal ion necessary to achieve a high level of diastereocontrol and the possible mechanism involved are discussed

  TiCl 3 / Py体系在无水THF中促进了苯基乙醛酸甲酯2与脂肪族和芳香族醛3的还原偶联。可以提供高收率（60-94％）和高顺-非对映选择性（高达85％）的α，β-二羟基酯4，其中讨论了实现高水平非对映控制所必需的金属离子上的配体类型及其可能的机理
• Enantioselective Equilibration−Access to Chiral Aldol Adducts of Mandelic Acid Esters
  作者：Stefan Scholtis、Andreas Ide、Rainer Mahrwald

  DOI：10.1021/ol062252w

  日期：2006.11.9

  [Structure: see text] Syn-configured aldol products of mandelic acid esters and aldehydes were synthesized by the catalytic use of amines in the presence of titanium(IV) tert-butoxide. Used along with chiral N-methylephedrine, anti-configured alpha,beta-dihydroxyesters were isolated with a high degree of enantioselectivity for the first time.

  [结构：见正文]在叔丁醇钛（IV）的存在下，通过胺的催化合成了扁桃酸酯和醛的顺式构筑的羟醛产物。与手性N-甲基麻黄碱一起使用时，首次以高对映选择性分离了抗构型的α，β-二羟基酯。
• Thiobenzoic Acid-Catalyzed Cα–H Cross Coupling of Benzyl Alcohols with α-Ketoacid Derivatives
  作者：Kaichi Sato、Hiromichi Egami、Yoshitaka Hamashima

  DOI：10.1021/acs.orglett.4c01594

  日期：2024.6.28

  The C–H alkylation of benzyl alcohols with α-ketoacid derivatives was achieved in the presence of thiobenzoic acid with or without Ru or Ir photoredox catalysts. The thiobenzoic acid serves as a photoexcited single-electron reducing reagent and a hydrogen atom transfer catalyst, while addition of the metal photoredox catalyst assists the electron transfer and improves the reaction efficiency. Various

  苯甲醇与 α-酮酸衍生物的 C-H 烷基化是在硫代苯甲酸存在下，在有或没有 Ru 或 Ir 光氧化还原催化剂的情况下实现的。硫代苯甲酸充当光激发单电子还原剂和氢原子转移催化剂，而金属光氧化还原催化剂的添加有助于电子转移并提高反应效率。各种官能团都能耐受反应条件，并且以良好到高产率生产了位阻二醇。